My Biggest Money Mistakes (And What I’m Changing)

Bailey Kramer shares a transparent personal and business update, including wins and regrets. He is pursuing a cash-out refinance on his first solo rental property bought for $115,000 at 8.5% interest, expecting to lower the rate to about 6.5%, pull out roughly $30,000, and keep the payment increase under $100, with plans to refinance another property next. On the downside, he is selling his Tesla Model 3, which he bought to reduce a large tax bill but now regrets due to high monthly costs and being upside down (owing about $30,000 on a $22,000–$25,000 value). He also regrets financing 50% of his fiancée Ellie’s engagement ring, now paid off. He shares that his South Africa/Mauritius honeymoon is booked largely using points, his done-for-you midterm rental service is growing with many experienced investors, he outlines a vision to partner on real-estate-related companies, notes podcast download growth, invites guests, and plans review incentives.00:00 Welcome and Format01:05 Cash Out Refi Win04:09 Tesla Debt Regret10:09 Honeymoon Plans11:18 Ring Financing Lesson13:56 Done For You Growth16:38 Big Vision and Hiring20:59 Podcast Community Push23:40 Wrap Up and Thanks